Women’s active and vital involvement in the economic life of medieval Ashkenaz has become an axiom of historical scholarship. Yet rabbinic texts suggest that legal norms significantly circumscribed women’s economic agency, or at least attempted to do so – particularly if they were married. In accordance with Talmudic law, which granted husbands control over family resources and limited the circumstances under which wives could make autonomous financial decisions, married women and widows throughout the medieval period were compelled to take oaths that they had not misused or embezzled their husbands’ assets, underscoring the fact that most of the ‘joint’ property they handled in the course of their marriages was not legally their own. So too, by the end of the thirteenth century prevailing legal decisors reversed earlier dispensations and barred married business women from repaying debts incurred without their husbands’ knowledge or from taking oaths to deflect claims of negligence, which posed a serious impediment to their legal and commercial activity. Nonetheless, throughout this era, rabbinic authorities repeatedly referenced women’s engagement in economic activities and acknowledged the ways in which this reality upended Talmudic categories and legally-entrenched assumptions concerning credibility, responsibility, agency, and trust. In light of these seeming contradictions, this paper will re-examine medieval Ashkenazi women’s involvement in commerce, moneylending, and related enterprises as well as the economic structure of families and communities; and it will reflect upon the imperfect and never entirely straightforward ways in which law and economics interact and impact one another.